Cu(OTf)2 Catalyzed Rapid Nucleophilic Substitution of Propargyl Alcohols

doi:10.6023/cjoc202403050

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (11): 3531-3540.DOI: 10.6023/cjoc202403050 Previous Articles Next Articles

NOTE

三氟甲磺酸铜(II)催化的炔丙醇快速亲核取代反应

张顺吉^*(), 刘会丽, 金云

淮北师范大学化学与材料科学学院安徽淮北 235000

收稿日期:2024-03-29 修回日期:2024-05-15 发布日期:2024-06-24
基金资助:
安徽高校自然科学研究(2022AH050409)

Cu(OTf)₂ Catalyzed Rapid Nucleophilic Substitution of Propargyl Alcohols

Shunji Zhang^*(), Huili Liu, Yun Jin

College of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000

Received:2024-03-29 Revised:2024-05-15 Published:2024-06-24
Contact: *E-mail:sjzhang@chnu.edu.cn
Supported by:
Natural Science Research Project of Anhui Educational Committee(2022AH050409)

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Abstract

The propargylation of various nucleophiles including indoles, phenol, anisole, enoxysilanes, and alcohols was rapidly achieved using catalytic copper(II) triflate. The reaction conditions are mild, allowing for quick reactions in an undried solvent and under atmospheric air. The desired products are obtained with good yields.

Key words: Cu(OTf)₂, catalysis, propargyl alcohol, velocity, nucleophilic substitution

Cite this article

Shunji Zhang, Huili Liu, Yun Jin. Cu(OTf)₂ Catalyzed Rapid Nucleophilic Substitution of Propargyl Alcohols[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3531-3540.

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Fig. & Tab. 3

References 20

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Entry	Condition	Yield/%
1	Cu(OTf)₂ (10 mol%), MeCN, r.t.	NR^a
2	Cu(OTf)₂ (10 mol%), MeCN, 70 ℃	90
3	Al(OTf)₃ (10 mol%), MeCN, 70 ℃	80
4	Fe(OTf)₃ (10 mol%), MeCN, 70 ℃	60
5	CuCl₂ (10 mol%), MeCN, 70 ℃	NR^a
6	CuI (10 mol%), MeCN, 70 ℃	NR^a
7	Cu(OTf)₂ (1 mol%), MeCN, 70 ℃	87
8	Cu(OTf)₂ (5 mol%), MeCN, 70 ℃	93
9	Cu(OTf)₂ (20 mol%), MeCN, 70 ℃	91

Entry	Condition	Yield/%
1	Cu(OTf)₂ (10 mol%), MeCN, r.t.	NR^a
2	Cu(OTf)₂ (10 mol%), MeCN, 70 ℃	90
3	Al(OTf)₃ (10 mol%), MeCN, 70 ℃	80
4	Fe(OTf)₃ (10 mol%), MeCN, 70 ℃	60
5	CuCl₂ (10 mol%), MeCN, 70 ℃	NR^a
6	CuI (10 mol%), MeCN, 70 ℃	NR^a
7	Cu(OTf)₂ (1 mol%), MeCN, 70 ℃	87
8	Cu(OTf)₂ (5 mol%), MeCN, 70 ℃	93
9	Cu(OTf)₂ (20 mol%), MeCN, 70 ℃	91

三氟甲磺酸铜(II)催化的炔丙醇快速亲核取代反应

Cu(OTf)₂ Catalyzed Rapid Nucleophilic Substitution of Propargyl Alcohols

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References 20

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Entry	Propargyl alcohol	Nuclephile	Product	Yield/%
1				93
2				86
3				85
4				96
5				93
6				93
7				90
8				88
9				92
10				88
11				85
12				86
13				85
14				80
15				87
16				91
17				85
18				93^b
19				92^b
20				87^b
21				79^b
22				80^b
23				84^b
24				98
25				97
26				90

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